How to Test Your Dream Job II (Case Study: Me as Kentucky Horserace Gambler)

“It’s been my experience that folks with no vices have very few virtues.”

-Abraham Lincoln


I never bet.

Well, usually not. I’ll never play craps or other games of chance, but I have bet on one type of sport in the past: UFC fights. And here’s the rub: I’ve never lost.

Late last week I traveled to the Bluegrass capital of the world — Kentucky — to hang out with Drew Curtis, CEO of, and decided to test my luck on a different sport: horse racing. The difference here, of course, is that I know a lot about fighting and absolutely nothing about horse racing.

The rub? I won cash on every race I personally put money on. I’ll tell you how I did it, but let’s begin at the beginning of the story…

Last Friday afternoon was perfect weather for seer sucker jackets and sun dresses. As we rolled into what many consider the best high-class racetrack in the world, Keeneland (where all the race scenes from Seabiscuit were filmed), everything was a first. Besides men in plaid pants, drive-through betting, and the best “whatever was left over from last night” stew on the planet, called “Burgoo” (the secret is pepper and bay leaves; I got a chef to spill the beans), there were a few other things that surprised me:

-The horses are implanted with GPS tracking devices in their heads to determine win order — and computerized replays — in close cases.

-The track is actually fake dirt, called PolyTrack, that looks like the emptied contents of a vacuum cleaner bag: synthetic fibers, recycled rubber, and silica, coated with wax and mixed with sand.

-The odds on a horse, and thus the potential return on a bet, are determined solely by what others bet; thus, the worst horse can appear to be the most likely to win if someone places money on it and other follow suit in mob reaction (or if the owner of another horse want to increase the ROI on his own horse by dropping his own horse’s odds).

Just as with anything, there are too many options and there is too much data. For a horse racing virgin — especially one being fed lots of fine bourbon — I was going to have to keep things simple. Here are a few things Drew, a damn smart cookie, taught me:

1. In the program, each race has the horses ranked by “handicapper” (what professional bettors, who watch practices and otherwise obsess on the sport, predict), “speed” (top speed, which is different from the average pace), and “class” (bloodline). If a horse is in all three, it’s a good bet in what’s called an “exactawheel” (explained below).

2. Don’t bet on a race unless there is a clear favorite winner. This keeps the “real” odds somewhat more predictable.

3. Don’t bet on a race if most horses haven’t been in races before, as there is no historical data, and practice stats aren’t reliable. I follow this same rule with fights. Competition changes all the numbers.

4. Some horses, even if they are the speed favorite, prefer to follow a lead horse and will slow down rather than take first place. Look for multiple second-place finishes as an indicator of this habit. Speed horses are also only potent in no-wind conditions.

5. A good jockey counts for a lot. Even though I rode quarterhorses for most of my youth and competed in barrel racing, I still don’t get this in a sprint race. I’m sure it makes a difference for some positioning, but that much? Apparently so. Drew always used to bet on a jockey named Pat Day, regardless of how crappy the horse was, and Pat won about 25% of the time. It was possible to hedge your bets and almost always come out ahead, so Drew was understandably pissed when Pat retired.

6. There are a million and one ways to place bets, but a few seemed better than others, so I focused on them:

a. Bet on number X to win if you have some form of proprietary knowledge: self-explanatory

b. Bet on a “follower” horse (explained above) for 2nd-place if it is the clear speed favorite with no wind.

b. Bet on number X to win and then “exactabox” number Y to place 2nd (“to place”) and number Z to place 3rd (“to show”), which means that you win if Y and Z come in in either order.

c. “Box” three horses for 1st, 2nd, and 3rd place. This means that if your chosen horses come in in any order in the top three positions, you win.

d. Place small bets on “trifectas” and “superfectas,” which are predicting the exact order of 1st-3rd place and 1st-4th place, respectively. Some math whizzes will place $10-12K in mini-bets on all of the possible superfecta permutations on specific races of the Kentucky Derby.


Me and Drew with Maker’s Mark bourbon and a bourbon-soaked cigar (I don’t smoke)


The Only Thing in Kentucky Not Fried or Covered with Cheese: “Burgoo�

So what happened? I didn’t win all of my bets, but I won money on all of the races I bet on. Most often, I would lose the “to-win” bet (what do I know?) but win a box or exactawheel for the first three positions. In one case, Drew and I won a superfecta.

On the last race of the day, I decided to strike out on my own and place an odd bet. Looking at race 10, there weren’t any clear favorites, but I had noticed a notation earlier in the day, “(L)”, which meant that it was the first time a horse had used Lasix in a race. From working with pro athletes and bodybuilders, I know that Lasix is a strong diuretic. I hypothesized that horses using it for the first time would either suffer organ failure or have a 15-20% performance improvement from decreased weight. I cross-referenced this “(L)” with the best-performing jockey from that group and placed a $5 bet on “Markdale” to win: a 27-to-1 underdog. I also placed three other $5 bets based on recommendations from handicappers and bookies.

Markdale won! I ended up pocketing slightly more than odds, so near $150, and that left me with a race profit of $130.


That horse is RIPPED! Thanks, Lasix!

It isn’t my next career, but with a few glasses of world-class bourbon and great weather, it was one hell of a weekend.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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16 Replies to “How to Test Your Dream Job II (Case Study: Me as Kentucky Horserace Gambler)”

  1. Nice Tim!

    Next up…I expect to see you hit up the halls of MIT, study with the whizkids and take Vegas for a ride as a blackjack pro!

    If you’ve read “Busting Vegas”…you know what I mean! It’s a great book and quick read.

    I’m working on my own “dream job”….well, not really job, but sport. Bodybuilding. There’s big show this weekend in my neck of the woods (Emerald City Classic in Seattle) and I am excited to watch (no, I’m not stepping on stage) and get some inspiration to carry through my first contest (which will be sometime next year….I have a LONG way to go..).

    Bodybuilding is the exact opposite thing that people would expect from my (I am a “former” Ironman triathlete), but I figure it would be a fun thing to try out.

  2. Ravi,

    “Bringing Down The House”, about the same group of MIT students, is one of my favorite books! Too bad the group blackjack approach has since been hacked by the casinos. Facial recognition spoils all the fun 😉

    If you are going for bodybuilding, keep an eye out for a post in the next week or two. I’ll be showing people (including photos and training) of how I gained 34 lbs. of muscle in 28 days (!).

    Thanks for the comment!

  3. FYI: “Busting Vegas” is by the same author as “Bringing Down The House”….but it is MUCH MORE extreme. It profiles a different goup of MIT Kids who use much more advanced techniques….makes the stuff they were doing in the first book look like child’s play!

    Not that I am condoning what they did (though their techniques were not illegal)….I do think it just shows how much power the human mind and ingenuity can have.

    As for bodybuilding….I am very eager to see your post. Gaining 34lbs of muscle in 28 days sounds very cool….though I am extremely skeptical that anything like that is possible. I know several bodybuilders and even those that have used every “cocktail” known to mail haven’t gained that fast.

    Happy to be proven wrong 🙂

  4. Hey,

    came across your blog looking for parimutuel betting tips… ALWAYS looking for tips! Man, “Busting Vegas” is my favorite book of all time! I play the horses at Delaware Park – by far one of the best horse racing tracks on the east coast. So far I’m up $7500 in the past year! I try to play a few rounds at the golf course there too but I suck. Anyway, I’m thinking about getting into Spread betting…. What do you think?

  5. Hi Mark,

    I’m afraid I know nothing of spread betting. All I know is in this post! Good luck, and may you take the Derby!



  6. aww.. i love Drew Curtis. i’ve been a fan of his site for many years. he was actually just featured on a KCRW news story on internet entrepreneurs. i was shocked at how little he pays himself each year.. 🙂 anyway, i just ‘stumbled’ across your site and am ingesting with veracity. hope life finds you well.

  7. i’ve only bet once. I got a superfecta i think its called. 20 to 1 odds. only it was close to the start and instead of betting $10, the clerk only bet $1.

    anyway, the $20 winnings was awesome!

  8. Hey Tim,

    Being quite familiar with betting the horses, try looking into trifecta part wheels. I don’t have the space and time to explain all of the ins and outs here, but basically you are picking a key horse and selecting a few other horses to go with your key horse. This is called a tri-part-wheel. Used to live in Perth, and played alot down there as well.



  9. Next time your in Lexington, Look me up. I know Drew as well.

    I run a from-home Search Marketing consultancy here. I escaped the Silicon Valley to live here and take more control over my life. Seth Godin considers me a “quitter” on his blog for his new book. I kinda started following your stuff as of the last book.

    Some good ideas, some stuff that’ll get you in trouble. I like that 🙂

  10. Hey Tim, I am the editor of and a fan of your book. I live 5 minutes from Keeneland, so the next time you come through Lexington hit me on email and I’ll treat you to some better food than Burgoo. (in exchange for some writing tips of course) 🙂

  11. Hey Tim,

    I find it hard to believe that you won a superfecta and didn’t tell us how much you won…so spill the beans! What were your odds and what did you take home??!

  12. Also, regarding math whizzes place mini-bets on all the permutations of a superfecta- there are 116,280 combinations in a twenty horse race- no one has that kind of time or money! Did you actually meet someone who has?

  13. Fascinating… it goes to show it’s not only who you know, but what THEY know. Thanks for the fun insights..


  14. As a Kentuckian I have grown up at Churchill Downs and my personal favorite, Keeneland. Anytime you want to bet at the track, I’ll be glad to show you the ropes. We need to get you going on Trifectas, Superfectas, Pick 3s, 4s, 5s and 6s, as well as part wheels and other tactics to increase your odds while decreasing your expenses! I have two gambling vices, horse races and craps. It’s a good thing the tracks are only open 4 months a year!